JPH08277276A - Isothiazolecarboxylic acid derivative and rice neck rot-controlling agent with the same as active ingredient - Google Patents

Abstract

PURPOSE: To obtain a new isothiazolecarboxylic acid derivative as a rice neck rot-controlling agent, long in the sustainability of its effect, and having effect stable to exogenous factors such as water leakages, etc. CONSTITUTION: This new compound is expressed by formula I (R is a 1-4C alkyl, benzyl or phenyl; X is H, a halogen, 1-4C alkyl, 1-4C alkoxyl, etc.; (n) is 1-3), e.g. N-ethyl-N-phenyl-3-methylisothiazole-5-carboxylic acid amide. The compound of formula I is obtained by reaction of an aniline derivative of formula II with an isothiazolecarboxylic acid derivative's halide of formula III (Y is Cl, Br or I) if needed in the presence of a base (e.g. pyridine) in a solvent (e.g. THF). Rice neck rot is controlled by applying an agrochemical containing the compound of formula I as active ingredient to pathogenic fungi or their habitats.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to novel isothiazolecarboxylic acid derivatives and rice blast control agents containing these as active ingredients.

[0002]

BACKGROUND OF THE INVENTION Rice blast is a disease with the highest yield loss among various diseases. The cause is largely due to abnormal weather such as low temperature in summer and heavy rain. However, it is also due to unreasonable cultivation of varieties vulnerable to blast disease and poor control due to labor shortage. Japanese Patent Laid-Open No. 5-59024 discloses that
A rice blast control agent containing an isothiazolecarboxylic acid derivative represented by the following general formula (2) (chemical formula 4) as an active ingredient is described.

[0003]

[Chemical 4] [In the formula, R ¹ is a hydrogen atom, a halogen atom, or a carbon number of 1 to 4.
Represents an alkyl group or an alkoxy group having 1 to 4 carbon atoms, R ² represents a hydrogen atom, a halogen atom or a nitro group, Z is a morpholino group, a piperidinyl group, OR ³ {wherein R ³ is a hydrogen atom or an alkali metal; Atom, an alkyl group having 1 to 4 carbon atoms or NHR ⁵ R ⁶ R ⁷ (R ⁵ , R ⁶ and R ⁷
Represents a hydrogen atom or an alkyl group having 1 to 4 carbon atoms. )}, Or NHR ⁴ (wherein R ⁴ is a hydrogen atom,
Represents a linear or branched alkyl group having 1 to 18 carbon atoms, a cycloalkyl group, a cycloalkenyl group, a dimethylamino group, a furfuryl group, an alkoxy group, an alkylthio group, a phenyl group or an alkyl group substituted with a halogen-substituted phenyl group. . ) Represents. However, when the compounds disclosed in the Examples of JP-A-5-59024 are used in paddy fields, the initial control effect is sufficiently high, but the effect gradually decreases over a long period after the chemical treatment. However, when there is a certain external factor, for example, downward movement of water due to water leakage or the like, there is a problem that the durability of the drug is further shortened.

[0004]

[Problems to be Solved by the Invention] Infection by blast fungus lasts for an extremely long period from the leaf blast stage to the panicle blast, and in the actual paddy field, various external factors affecting the effect of the drug, particularly water leakage. There is also a problem such as the disappearance of the drug due to the downward movement of water. Therefore, it is an object of the present invention to provide a drug which has an excellent controlling effect against rice blast, has a long duration of effect, and exhibits a stable effect against external factors such as water leakage.

[0005]

Means and Actions for Solving the Problems The present inventors have conducted research on isothiazolecarboxylic acid derivatives in order to solve these problems, and as a result, the above-mentioned Japanese Patent Laid-Open No.
The novel isothiazolecarboxylic acid derivative, which is not disclosed in JP-A-59024, is extremely excellent as a control agent for rice blast, has a long-lasting effect, and has a stable effect against external factors such as water leakage. The present invention has been completed by discovering that it has an excellent feature of showing. That is, the present invention provides the compound represented by the general formula (1)

[0006]

Embedded image (In the formula, R represents an alkyl group having 1 to 4 carbon atoms, an optionally substituted benzyl group, an optionally substituted phenyl group,
X represents a hydrogen atom, a halogen atom, an alkyl group having 1 to 4 carbon atoms, an alkoxy group having 1 to 4 carbon atoms, an alkylthio group having 1 to 4 carbon atoms or a trifluoromethyl group, and n is 1
Represents an integer of 3; ), An isothiazolecarboxylic acid derivative, a rice blast control agent containing the same as an active ingredient, and a method for controlling rice blast, which comprises applying the agent to a pathogenic bacterium or its habitat.

Specific examples of the substituent R of the isothiazolecarboxylic acid derivative represented by the above general formula (1) include hydrogen atom; methyl group, ethyl group, propyl group, isopropyl group, butyl group, s-butyl group. Or an alkyl group having 1 to 4 carbon atoms such as t-butyl group; a benzyl group which may be substituted such as benzyl group, 4-chlorobenzyl group, 3-methoxybenzyl group or 2-methylbenzyl group; phenyl group, Examples thereof include an optionally substituted phenyl group such as a 3-chlorophenyl group, a 2-methoxyphenyl group or a 4-tolyl group.

On the other hand, specific examples of X include hydrogen atom; halogen atom such as fluorine atom, chlorine atom, bromine atom or iodine atom; methyl group, ethyl group, propyl group, isopropyl group, t-butyl group and the like. An alkyl group having 1 to 4 carbon atoms; an alkoxy group having 1 to 4 carbon atoms such as methoxy group, ethoxy group or propoxy group; an alkylthio group having 1 to 4 carbon atoms such as methylthio group, ethylthio group or butylthio group; or trifluoro Examples include a methyl group.

The isothiazolecarboxylic acid derivative represented by the general formula (1) of the present invention is a novel compound and can be produced, for example, by the following (method A) or (method B) (chemical formula 6).

[0010]

[Chemical 6] (In the formula, R, X, and n have the above-mentioned meanings, and Y represents a chlorine atom, a bromine atom, or an iodine atom.) That is, in (A method), various anilines represented by the formula (3) It can be produced by reacting the derivative with a halide of the isothiazolecarboxylic acid derivative represented by the formula (4) in a molten state or in a solvent.

The solvent used in the reaction in the method (A) may be any solvent inert to the reaction, for example, aliphatic hydrocarbons such as hexane and petroleum ether, and aromatic hydrocarbons such as benzene, toluene, chlorobenzene and anisole. Kind,
Dioxane, tetrahydrofuran, ethers such as diethyl ether, acetonitrile, nitriles such as propionitrile, ethyl acetate, esters such as butyl acetate, dichloromethane, chloroform, halogenated hydrocarbons such as 1,2-dichloroethane, dimethylformamide, Examples thereof include aprotic solvents such as dimethyl sulfoxide and N, N-dimethylimidazolidinone, and mixed solvents thereof can also be used.

This reaction may also be carried out in the presence of a base, and as the base, for example, hydroxides of alkali metals and alkaline earth metals such as sodium hydroxide, potassium hydroxide and calcium hydroxide; calcium oxide, oxidation Alkali metal and alkaline earth metal oxides such as magnesium; Alkali metal and alkaline earth metal hydrides such as sodium hydride and calcium hydride; Alkali metal amides such as lithium amide and sodium amide; Sodium carbonate and carbonate Carbonates of alkali metals and alkaline earth metals such as potassium, calcium carbonate, magnesium carbonate;
Alkali metal and alkaline earth metal hydrogen carbonates such as sodium hydrogen carbonate and potassium hydrogen carbonate; alkali metal alkyls such as chill lithium, butyl lithium, phenyl lithium and methyl magnesium chloride; sodium methoxide, sodium ethoxide, potassium-t. −
Alkyl metal and alkaline earth metal alkoxides such as butoxide, dimethoxymagnesium; organic bases such as triethylamine, pyridine, N, N-dimethylaniline, N-methylpiperidine, lutidine, 4- (N, N-dimethylamino) pyridine And triethylamine and pyridine are particularly preferable. The amount of these bases to be used is not particularly limited, but preferably 5 mol% to 20 mol% in excess with respect to the thiazolecarboxylic acid halide represented by the formula (3).

The various anilines represented by the general formula (3) and the isothiazolecarboxylic acid halide represented by the formula (4) are generally used in equimolar amounts. May be used in excess of 1 mol% to 20 mol% with respect to the other. The reaction temperature is 0 to 150 ° C.,
It is preferably 0 to 40 ° C.

The method (B) can be produced by reacting the carboxylic acid anilide represented by the formula (5) with various alkylating agents in the presence of a base. Specific examples of the alkylating agent used include alkyl halides such as methyl iodide, ethyl bromide, isopropyl bromide, butyl chloride and isopropyl iodide; benzyl chloride, 4-
Examples thereof include, but are not limited to, benzyl halides such as chlorobenzyl bromide; and sulfuric acid esters such as dimethyl sulfate and diethyl sulfate.

The solvent used in this alkylation reaction may be any solvent inert to the reaction, for example, aliphatic hydrocarbons such as hexane and petroleum ether; aromatics such as benzene, toluene, chlorobenzene and anisole;
Ethers such as dioxane, tetrahydrofuran, diethyl ether; ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone; aprotic solvents such as dimethylformamide, dimethyl sulfoxide, N, N-dimethylimidazolidinone, and the like. Mixed solvents are also used.

Examples of the base used in this reaction include hydroxides of alkali metals and alkaline earth metals such as sodium hydroxide, potassium hydroxide and calcium hydroxide; alkali metals such as calcium oxide and magnesium oxide, alkaline earth. Oxides of group metals; hydrides of alkali metals and alkaline earth metals such as sodium hydride and calcium hydride; amides of alkali metals such as lithium amide and sodium amide; sodium carbonate, potassium carbonate, calcium carbonate, magnesium carbonate, etc. Alkali metal and alkaline earth metal carbonates; sodium hydrogen carbonate, potassium hydrogen carbonate and other alkali metal and alkaline earth metal hydrogen carbonates; methyl lithium, butyl lithium, phenyl lithium, methyl magnesium chloride and other alkali metal alkyls Sodium methoxide, sodium ethoxide, potassium -t- butoxide, alkoxides of alkali metals and alkaline earth metals such as dimethoxy magnesium; triethylamine, pyridine, N, N-
Dimethylaniline, N-methylpiperidine, 1,8-diazabicyclo [5.4.0] undecene-7 (DB
U), 4- (N, N-dimethylamino) pyridine, and other organic bases.

The drug thus obtained, which contains the compound of the present invention as an active ingredient, has an excellent action-controlling effect on rice blast disease, and the effect lasts for a long period of time after being treated in rice fields. .

The compounds of the present invention are isothiazole-5-
The above-mentioned JP-A-5-59024 in that various anilino groups are introduced into the amino group of the carboxylic acid amides.
Different from the compounds described in the publication. In improving the performance as a blast control agent, the significance that the amino group of the amide is various anilino groups is significant, and when the compound of the present invention is applied to rice blast, as will be apparent from the test examples described below. It has excellent characteristics that it is extremely excellent as a control agent for blast disease, has a long-lasting effect, and exhibits a stable effect against external factors such as water leakage.

The agricultural and horticultural fungicides of the present invention can be used not only as a mixture with other fungicides, insecticides, herbicides, plant growth regulators and other pesticides, soil improvers or fertilizers, but also these. Mixed preparations with are also possible.

The compounds of the invention may be used as such, but are preferably applied in the form of a composition in admixture with a carrier, which may include a solid or liquid diluent. As used herein, the term carrier means a synthetic or natural inorganic or organic substance formulated to help the active ingredient reach the site to be treated and to facilitate the storage, transport, and handling of the active ingredient compound. .

Suitable solid carriers include clays such as montmorillonite, kaolinite and bentonite, diatomaceous earth, clay, talc, vermiculite, gypsum, calcium carbonate, silica gel, inorganic substances such as ammonium sulfate, soybean powder,
Examples include vegetable organic substances such as sawdust and flour, and urea.

Suitable liquid carriers include aromatic hydrocarbons such as toluene, xylene and cumene, paraffinic hydrocarbons such as kerosene and mineral oil, halogenated hydrocarbons such as carbon tetrachloride, chloroform and dichloroethane, and acetone. , Ketones such as methyl ethyl ketone, ethers such as dioxane, tetrahydrofuran and diethylene glycol dimethyl ether, alcohols such as methanol, ethanol, propanol and ethylene glycol, dimethylformamide, dimethyl sulfoxide and water. Furthermore, in order to enhance the efficacy of the compound of the present invention, the following auxiliary agents can be used alone or in combination depending on the purpose in consideration of the dosage form of the preparation, the application scene and the like.

As the auxiliary agent, for the purpose of emulsification, dispersion, spreading, wetting, binding, stabilization, etc., lignin sulfonate, alkylbenzene sulfonate, alkyl sulfate ester salt, polyoxyalkylene alkyl sulfate salt, and poly Anionic surfactants such as oxyalkylene alkyl phosphate salts, polyoxyalkylene alkyl ethers, polyoxyalkylene alkyl aryl ethers, polyoxyalkylene alkyl amines, polyoxyalkylene alkyl amides, polyoxyalkylene alkyl thioethers, polyoxyalkylene fatty acid esters , Glycerin fatty acid ester, sorbitan fatty acid ester, polyoxyalkylene sorbitan fatty acid ester, and polyoxypropylene polyoxyethylene block polymer On surfactant, calcium stearate, lubricants such as wax, stabilizers such as isopropyl hydroperoxide diene phosphate, other cellulose, carboxymethyl cellulose, casein, gum arabic, and the like. However, these components are not limited to those described above.

The amount of the active ingredient of the compound of the present invention is usually 0.5 to 20% by weight for powders, 5 to 50% by weight for emulsions, 10 to 90% by weight for wettable powders, and 0.1 to 20 for granules. %, And 10-90% by weight for flowable formulations. On the other hand, the amount of the carrier in each dosage form is usually 60 to 99% by weight for powders and 10 to 90% by weight for wettable powders.
Granules are 80 to 99% by weight, emulsions are 40 to 95% by weight, flowable formulations are 10 to 90% by weight, and the amount of auxiliary agent is usually 0.1 to 20% by weight for powders and 1 to 20% for emulsions. 20% by weight, 0.1-20% by weight of wettable powder,
Granules are 0.1 to 20% by weight, and flowable formulations are 0.1 to 20% by weight.

[0025]

EXAMPLES The present invention will be described in more detail below with reference to examples and test examples. Example 1. Synthesis of N-ethyl-N-phenyl-3-methylisothiazole-5-carboxylic acid amide (Compound No. 9): Method (A) 1.0 g of 3-methylisothiazole-5-carboxylic acid together with 3 ml of thionyl chloride was added to 1 The mixture was heated under reflux for 5 hours and concentrated under reduced pressure to prepare a carboxylic acid chloride. This is dissolved in 10 ml of tetrahydrofuran and 1.0 g of pyridine
Was added, a solution of 0.75 g of N-ethylaniline in 1 ml of tetrahydrofuran was added, and the mixture was stirred at room temperature for 1 hour. The reaction solution was discharged into ice water and extracted with ethyl acetate. The organic layer was washed successively with diluted hydrochloric acid and saturated aqueous sodium hydrogen carbonate solution, and dried over magnesium sulfate. Concentrate the solvent under reduced pressure,
The crystals were washed with hexane to obtain 0.84 g of the desired product (yield 55%). Melting point: 46-48 ° C

Example 2. Synthesis of N-methyl-N- (4-chlorophenyl) -3-methylisothiazole-5-carboxylic acid amide (Compound No. 5): (B) method 3-methylisothiazole-5-carboxylic acid 1.0 g
The carboxylic acid chloride prepared in the same manner as in Example 1 was dissolved in 10 ml of tetrahydrofuran, 1.0 g of pyridine was added, then a solution of 0.7 g of 4-chloroaniline in 1 ml of tetrahydrofuran was added, and the mixture was stirred at room temperature for 1 hour. The reaction solution was discharged into ice water and extracted with ethyl acetate,
The organic layer was washed with dilute hydrochloric acid and a saturated aqueous sodium hydrogen carbonate solution in that order, and dried over magnesium sulfate. After that, the solvent was concentrated under reduced pressure, and an intermediate N- (4-chlorophenyl)-
3-Methylisothiazole-5-carboxylic acid amide
96 g was obtained (68% yield). This intermediate was dissolved in 10 ml of tetrahydrofuran, 0.18 g of sodium hydride (60% oil product) was added under a nitrogen stream, and after 15 minutes, 2.7 g of methyl iodide was added and stirred at room temperature for 1 hour. The reaction solution was discharged into ice water, extracted with ethyl acetate, and dried over magnesium sulfate. Then, the solvent was concentrated under reduced pressure to obtain 0.68 g of the desired product (yield 67%). Melting point: 75 to 77 ° C. Table 1 (Tables 1 and 2) shows compounds synthesized in the same manner as in Examples 1 and 2.

[0027]

[Table 1]

[0028]

[Table 2] These compounds may be used as they are, but they are more effective when formulated. The formulation example is shown below,
These are some of them. In the following, "parts" means "parts by weight".

Formulation Example 1 Granules N-methyl-N-phenyl-3-methylisothiazole-5-carboxylic acid amide (Compound No. 1) 5 parts, bentonite 22 parts, talc 70 parts, Solpol 5060 (surfactant: Toho Chemical Co., Ltd. (trade name) 3 parts and a small amount of antifoaming agent were uniformly kneaded, granulated by a basket granulator and dried to obtain 100 parts of granules.

Formulation Example 2 Granules N-methyl-N- (4-tolyl) -3-methylisothiazole-5-carboxylic acid amide (Compound No. 3) 5 parts,
Bentonite 60 parts, talc 31 parts, sodium dodecylbenzene sulfonate 1 part, polyoxyethylene alkyl allyl ether 1 part, and lignin sulfonate sodium 2
After mixing the parts, an appropriate amount of water was added and uniformly kneaded, granulated by a basket granulator, and dried to obtain 100 parts of granules.

Formulation Example 3 Granules N-methyl-N- (4-methoxyphenyl) -3-methylisothiazole-5-carboxylic acid amide (Compound No. 4) 5 parts, bentonite 35 parts, talc 57 parts, lignin sulfone After mixing 2 parts of acid soda and 1 part of sodium dodecylbenzene sulfonate, an appropriate amount of water was added and uniformly kneaded, granulated by a basket granulator and dried to obtain 100 parts of granules.

Formulation Example 4 Granules N-methyl-N- (4-chlorophenyl) -3-methylisothiazole-5-carboxylic acid amide (Compound No. 5) 5 parts, bentonite 60 parts, clay 32 parts, alkylbenzene sulfonic acid After mixing 3 parts of soda, an appropriate amount of water was added and uniformly kneaded, granulated by a basket granulator and dried to obtain 100 parts of granules.

Formulation Example 5 Granules N, N-diphenyl-3-methylisothiazole-5-
Carboxylic amide (Compound No. 10) 3 parts, clay 9
3.7 parts, 0.2 parts of dialkyl sulfosuccinate, 0.1 part of sodium alkyl sulfate ester, and 3.0 parts of sodium polycarboxylic acid were uniformly kneaded, granulated with a basket granulator and then dried. To obtain granules.

Formulation Example 6 Granules N-methyl-N- (3-chlorophenyl) -3-methylisothiazole-5-carboxylic acid amide (Compound No. 6) 3 parts, clay 93.5 parts, dialkylsulfosuccinate 0 .5 parts, and carboxymethyl cellulose 3
After mixing the parts, an appropriate amount of water was added and kneaded, and the mixture was granulated and dried by a usual method using a granulator to obtain 100 parts of granules.

Formulation Example 7 Wettable powder N-methyl-N- (2-chlorophenyl) -3-methylisothiazole-5-carboxylic acid amide (Compound No. 7) 50 parts, calcium carbonate 40 parts, Solpol 503
9 parts (mixture of anionic surfactant and white carbon: trade name of Toho Chemical Co., Ltd.) and 5 parts of white carbon were uniformly mixed and pulverized to obtain a wettable powder.

Formulation Example 8 Wettable powder N-methyl-N- (3,4-dichlorophenyl) -3-
Methylisothiazole-5-carboxylic acid amide (Compound No. 8) 70 parts, kaolinite 25 parts, Solpol 50
3 parts of 39 (mixture of anionic surfactant and white carbon: trade name of Toho Chemical Co., Ltd.) and 2 parts of white carbon were uniformly mixed and pulverized to obtain a wettable powder.

Formulation Example 9 Wettable powder N-Ethyl-N-phenyl-3-methylisothiazole-5-carboxylic acid amide (Compound No. 9) 50 parts, calcium carbonate 40 parts, Sorpol 5039 (with anionic surfactant White carbon mixture: Toho Chemical Co., Ltd.
5 parts of the product name) and 5 parts of white carbon were uniformly mixed and pulverized to obtain a wettable powder.

Formulation Example 10 Wettable powder N, N-diphenyl-3-methylisothiazole-5-
70 parts of carboxylic acid amide (Compound No. 10), 25 parts of kaolinite, 3 parts of Solpol 5039 (mixture of anionic surfactant and white carbon: trade name of Toho Chemical Co., Ltd.), and 2 parts of white carbon are uniformly mixed. It was crushed to obtain a wettable powder.

Formulation Example 11 Emulsion N, N-diphenyl-3-methylisothiazole-5-
Carboxylic amide (Compound No. 10) 20 parts, Solvesso 150 (Exxon Chemical Co., Ltd.) 75 parts, Solpol 2
An emulsion was prepared by uniformly mixing 5 parts of 680 (surfactant).

Formulation Example 12 Flowable agent N-methyl-N-phenyl-3-methylisothiazole-5-carboxylic acid amide (Compound No. 1) 40 parts, Solpol 3353 (nonionic surfactant: Toho Kagaku Co., Ltd.) Trade name) 5 parts, 5% 1% aqueous solution of xanthan gum,
In 40 parts of water and 10 parts of ethylene glycol, components other than the active ingredient are uniformly dissolved, and then the compound of the present invention is added.
After stirring well, wet pulverization was performed with a sand mill to obtain a flowable agent.

Formulation Example 13 Powder N-methyl-N- (4-tolyl) -3-methylisothiazole-5-carboxylic acid amide (Compound No. 3) 10
Parts and 90 parts of clay were uniformly mixed to obtain a dust.

Formulation Example 14 Dust powder N-methyl-N- (4-methoxyphenyl) -3-methylisothiazole-5-carboxylic acid amide (Compound No. 4) 5 parts, clay 40 parts, talc 54 parts, calcium stearate 1 Parts were crushed and mixed to obtain a powder.

It will be specifically described with reference to test examples that the rice blast control agent according to the present invention exhibits excellent rice blast control effect. Test Example 1 Rice blast control effect test (under seedling box treatment, non-leakage conditions) Rice seedlings (variety: Mangetsumochi; 2 leaf stage) grown in a rice seedling box (30 cm x 60 cm x 3 cm) were prepared according to Formulation Example 2. The adjusted granules were processed so that the amount per box was predetermined.
After 3 days, it was transplanted to a Wagner pot of 1/5000 are and grown in a greenhouse. Every 30 days, 45 days, and 60 days after transplantation, 1/3 of all treated pots are used, sprayed and inoculated with the spore suspension each time, and placed for 1 week under high humidity conditions at a temperature of 25 ° C, The number of lesions was investigated, and the duration of effect was examined. The control value was calculated by the following formula (Equation 1). The results are shown in Table 2 (Table 3). (6 repetitions)

[0044]

[Equation 1] Control value = (1-number of lesions in treated group / number of lesions in untreated group) × 100

[0045]

[Table 3] Control compound: N-benzyl-3-methyl-5-isothiazolecarboxylic acid amide (compound described in JP-A-5-59024)

Test Example 2 Rice blast control effect test (under seedling box treatment, water leakage condition after transplantation) Formulation example for rice seedlings (variety: mangetsumochi; 2 leaf stage) grown in a rice seedling box (30 cm × 60 cm × 3 cm) The granules prepared according to 2 were treated so that a predetermined amount per box was obtained.
After 3 days, it was transplanted to a Wagner pot of 1/5000 are and grown in a greenhouse. Every 30 days, 45 days, and 60 days after transplantation, 1/3 of all treated pots are used, and the spore suspension is sprayed and inoculated each time, and the pots are kept at 25 ° C for 1 week under high humidity conditions. , The number of lesions was investigated, and the duration of the effect was examined. The water leakage condition was 1.5 cm / day.
The control value was calculated by the following formula (Equation 2). The results are shown in Table 3 (Table 4). (6 repetitions)

[0047]

[Equation 2] Control value = (1-number of lesions in treated plot / number of lesions in non-treated plot) × 100

[0048]

[Table 4] Control compound: N-benzyl-3-methyl-5-isothiazolecarboxylic acid amide (compound described in JP-A-5-59024)

Test Example 3 Rice blast control effect test (water application, non-leakage condition) Rice (variety: Mangetsumochi; 3 leaf stage) was transplanted to a Wagner pot of 1/5000 are and grown in a greenhouse for 1 week. After that, the granules prepared according to Formulation Example 2 were applied to the surface of the water in a predetermined amount per are. Drug treatment 30 days, 40
Each day, every 50 days, one-third of all treated pots are used, sprayed with a spore suspension each time, and kept at 25 ° C for 1 week under high humidity conditions. Investigate,
The duration of the effect was investigated. The control value was calculated by the following formula (Equation 3). The results are shown in Table 4 (Table 5). (6 repetitions)

[0050]

[Equation 3] Control value = (1-number of lesions in treated plot / number of lesions in non-treated plot) × 100

[0051]

[Table 5] Control compound: N-benzyl-3-methyl-5-isothiazolecarboxylic acid amide (compound described in JP-A-5-59024)

Test Example 4 Rice blast control effect test (water application, water leakage condition after chemical treatment) Rice (cultivar: Mangetsumochi; 3 leaf stage) was transplanted to a Wagner pot of 1/5000 are and placed in a greenhouse 1 After being grown for a week, the granules prepared according to Formulation Example 2 were applied to the surface of the water in a predetermined amount per are. Drug treatment 30 days, 40
Each day, every 50 days, one-third of all treated pots are used, sprayed with a spore suspension each time, and kept at 25 ° C for 1 week under high humidity conditions. Investigate,
The duration of the effect was investigated. The water leakage condition is 1.5 cm /
It was done on day. The control value was calculated by the following formula (Equation 4). The results are shown in Table 5 (Table 6). (6 repetitions)

[0053]

[Equation 4] Control value = (1-number of lesions in treated group / number of lesions in untreated group) × 100

[0054]

[Table 6] Control compound: N-benzyl-3-methyl-5-isothiazolecarboxylic acid amide (compound described in JP-A-5-59024)

[0055]

EFFECTS OF THE INVENTION The isothiazolecarboxylic acid derivative according to the present invention has an extremely excellent effect on controlling rice blast disease, has a long-lasting effect, and is stable against external factors such as water leakage. Therefore, it is useful as a fungicide for agricultural and horticultural use.

 ─────────────────────────────────────────────────── ─── Continued Front Page (72) Inventor Naofumi Tomura 1144 Togo Togo, Mobara-shi, Chiba Mitsui Toatsu Chemical Co., Ltd.

Claims (4)

[Claims] 1. A general formula (1) (Chemical Formula 1): (In the formula, R represents an alkyl group having 1 to 4 carbon atoms, an optionally substituted benzyl group, or an optionally substituted phenyl group, and X is a hydrogen atom, a halogen atom, or an alkyl group having 1 to 4 carbon atoms. Group, an alkoxy group having 1 to 4 carbon atoms, and 1 to carbon atoms
4 represents an alkylthio group or a trifluoromethyl group, and n represents an integer of 1 to 3. ) Isothiazolecarboxylic acid derivative represented by. 2. The compound according to claim 1, wherein in the general formula (1), R is a methyl group and X _n is a hydrogen atom. 3. General formula (1) (Chemical formula 2) (In the formula, R represents an alkyl group having 1 to 4 carbon atoms, an optionally substituted benzyl group, or an optionally substituted phenyl group, and X is a hydrogen atom, a halogen atom, or an alkyl group having 1 to 4 carbon atoms. Group, an alkoxy group having 1 to 4 carbon atoms, and 1 to carbon atoms
4 represents an alkylthio group or a trifluoromethyl group, and n represents an integer of 1 to 3. ) A rice blast control agent containing an isothiazolecarboxylic acid derivative represented by the formula (1) as an active ingredient. 4. The general formula (1) (formula 3): (In the formula, R represents an alkyl group having 1 to 4 carbon atoms, an optionally substituted benzyl group, or an optionally substituted phenyl group, and X is a hydrogen atom, a halogen atom, or an alkyl group having 1 to 4 carbon atoms. Group, an alkoxy group having 1 to 4 carbon atoms, and 1 to carbon atoms
4 represents an alkylthio group or a trifluoromethyl group, and n represents an integer of 1 to 3. ) A rice blast control method comprising applying a rice blast control agent containing an isothiazolecarboxylic acid derivative represented by the formula (4) as an active ingredient to a pathogen or its habitat.